Hydrochloric Acid → (5-{7-(Benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}-1,3,4-thiadiazol-2-yl)methanol

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Reaction Steps

Ethyl 5-{7-(benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}-1,3,4-thiadiazole-2-carboxylate (230 mg) was dissolved in a mixed solvent of tetrahydrofuran (8 mL)-methanol (2 mL), sodium borohydride (32 mg) was added under ice-cooling, and the mixture was stirred for 40 min. Water and 1M hydrochloric acid were added to the reaction mixture, and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, filtrated, and concentrated under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (ethyl acetate:hexane=10:90 to 90:10, volume ratio) to give the title compound (220 mg, yield 100%) as a pale-yellow solid. The obtained pale-yellow solid was recrystallized from ethyl acetate-diethyl ether to give pale-yellow crystals. melting point 159-160° C. MS 508 (MH+).

Provenance & Evidence